Jaclyn and Dave decided to take a mystery honeymoon after spending several months researching options and struggling to pick a destination.

“The moment we decided to go for it, we were sitting eating lunch at a restaurant on a very rainy day,” they said. “We had been talking about our honeymoon for a long time, and both of us looked at each other and realized that even if we spent our entire honeymoon inside a restaurant while it rained outside, it didn’t matter—we would be together. So we decided what the heck! We’ll go on a mystery honeymoon. We had so much on our plate trying to plan our wedding that we decided to delegate the most important part to the experts.”

So, in late June 2014, they headed to the Boston airport, ripped open their mystery packet, and discovered they were going to…the Azores in Portugal!

MMT: What were your top hopes about your destination and what your trip would include?D&J: Mostly we wanted a lot of relaxing coupled with a lot of activities. We aren’t the easiest couple to please—we can’t sit still, except when we want to, so I think we just filled our questionnaire with everything we could possibly think of. We definitely wanted a multi-destination trip (read above: can’t sit still), beach time (but not the whole time), and an active vacation. We wanted to go outside of the continental U.S. and were hoping to go to a different country altogether. We are very resourceful, so we didn’t need a lot of direction, just a few benchmarks throughout the trip to ensure we were taking as much advantage as possible.

Did you have a hard time waiting in anticipation to find out where you were going?With planning our wedding coinciding with our honeymoon, we really didn’t have a hard time. We had a lot of fun with it—a guessing game at our wedding, and all our friends and family got in on guessing for months beforehand. We honestly didn’t have that much time to think about the trip because we were so immersed in wedding planning. Toward the end, we definitely got anxious to know and started thinking much more about it in the last two weeks, but we were determined not to open it until the last possible minute. We even asked Alicia to put our initial trip (Philly to Boston) in a separate envelope so we could wait until we had to check in for our honeymoon flight at the check-in desk. I think our families were more anxious than us, and they definitely threatened to bribe MMT and to find our envelope with our itinerary and open it before us.

I heard something cool about a map at your wedding reception. How did you incorporate your mystery honeymoon into your wedding festivities?This was Dave’s idea. We are very traditional and had a pretty traditional wedding, while trying also to make it “our own.” One thing that was so unique about our wedding was our mystery honeymoon. So, we figured that we should memorialize it. We found a map online that was big enough for our 150 wedding guests to write on. Then we mounted it and made some quick instructions asking our guests to guess where we were going on our honeymoon on the actual map. We put it next to the guest book so people could easily leave their guess. We looked at the map the day after our wedding, before leaving on our honeymoon. We’re going to frame it and hang it in our house just to remember all the great guesses!

What were some of the guesses?We thought southern Spain/southern France or Greece; once we saw the packing list/weather outlook, we thought maybe Croatia. Our guests’ guesses were pretty concentrated in Europe and South America—and we had someone guess the Azores! Some folks knew more than others about what we had put on our questionnaire, so we didn’t get a large concentration in the Caribbean because we specifically asked to not have an all-inclusive resort or to be on the beach the whole time.

Tell me about your trip! What was your favorite part?The trip was amazing—everything we asked for and so much more. There was no best part! We had the best time, the greatest 10 days of our life. We landed in Ponta Delgado, Sao Miguel at 7 a.m. super sleepy and somehow made our way through Customs and onto another plane to another island (Pico) within about 45 minutes. We were taking everything in and so excited. On Pico, we stayed in a three-bedroom house all by ourselves—we got to cook and relax. We climbed Pico Mountain and tasted the wine of the island. We did a lot of sightseeing, and the people who ran the company who rented our house were so helpful! They basically gave us a three-day itinerary, complete with all the best restaurants on the island to try. We made it to the next island, Faial, in the middle of our trip, and we had so much fun there, too! It was totally different—a swanky hotel and basically a mini city. We got to go to the beach, bike down a volcano, and enjoy the local culture. Horta, the city we stayed in, is a sailing village, so we got to really experience that culture while there. We loved being in Horta because we could come and go to and from our hotel as we pleased. On the other islands, we really got to explore because we had a car, but it was a lot of daylong outings. In Horta, we were much more spontaneous for a few days! The last third of our trip was spent back in Ponta Delgado, Sao Miguel. We stayed in a bed and breakfast, which was really quaint and beautiful. We went to the hot springs full of iron and had the most wonderful local cuisine of food cooked in the ground near the hot springs. We did a lot of relaxing at the pool here toward the end of the trip and genuinely enjoyed the “big city” of the Azores.

What’s the best thing about mystery travel?It’s so exciting! You have to figure it out on your own and don’t have the ability to preplan at all. You have to be really spontaneous and be willing to roll with the punches. It is such an amazing experience to share with your new spouse and something we will really cherish for our lifetime. It’s also a great learning experience because of all the above mentioned aspects. You learn to trust each other and to trust the people who make your vacation spot their home and you look to them for guidance on your activities/food choices, etc.

What would you say to another engaged couple considering a mystery honeymoon, and why?Absolutely go for it! A lot of people will tell you that you are crazy and they could never do such a thing. But when it comes down to it, ask yourself the question: Why would I not have the experts plan my trip? It’s the ultimate form of delegation. You are going to have the florist create bouquets and centerpieces, you are going to have a tailor make your dress/tux/suit perfect, you are going to have a chef cook your wedding meal…why would you not have a travel company plan your honeymoon?! As long as you enjoy spending time together, you really can’t go wrong. If you honestly fill out the questionnaire (and you have to be honest!), you will get exactly what you wanted and so much more. It is so exciting to wake up the morning after your wedding and be super excited to find out where you are going on your honeymoon! It just keeps the excitement going. Plus, if your honeymoon wasn’t on the list of places you most want to visit, you can still have MMT plan your next trip to your destination of choice, and you might just get to explore someplace new.

In late June 2014, Cheryl was ready for a few days away from the chaos at work and for a chance to relax and enjoy her birthday. With her Magical Mystery Tours reveal packet in hand, she showed up to Washington Dulles airport and discovered she was headed to Nantucket, Massachusetts for an island retreat amid beautiful landscapes and a plethora of activities.

MMT: Why mystery travel?Cheryl: I wanted to commemorate a significant birthday. I had planned on going alone, but couldn’t decide where I wanted to go. Work was so hectic, with long hours, etc., and I couldn’t find the time to plan. I was at the point where I NEEDED, not wanted, to get away, but just didn’t know where to go. That’s where MMT entered the picture.

What were you looking for out of this trip?I was looking for some R&R, time to reflect, and a new adventure, though I suppose just the act of going through the MMT process and arriving at the airport with the unopened envelope in hand was half of the adventure…and definitely half of the fun! Several people who knew what I was doing said I was brave, but I never once felt that term applied. I am the type who typically plans, schedules, verifies, and reconfirms. This trip was going to be the opposite, and I was determined to go with the flow, even if it turned out to be a bad experience. It was going to be memorable…regardless!

Were you surprised when you opened your reveal packet at the airport?When I opened the envelope, my first thought was, “I was way off base!” Because of the weather forecast provided earlier, I couldn’t help but speculate where I might be going—and was wrong on all counts. I was expecting to see the Pacific Northwest (maybe Seattle, Portland, perhaps southern Canada), Upper Northwest (maybe Maine or southern Canada), or Alaska. I know I must have looked like a crazy lady waiting in the security line and finally walking to my gate in the Washington Dulles Airport—I just could not stop smiling. It was such a joyful experience.

How do you choose destinations when planning trips yourself?I have had the opportunity to travel a fair amount both in and out of country. I thoroughly enjoy traveling to new places and experiencing different cultures. It’s more of an adventure if English is not the native language. However, since I would be traveling alone on this trip and could allot only five days, I felt I would have a better experience without working through language barriers.

Tell me about your mystery trip! What was the best thing you did?I was as honest with myself as possible in completing the MMT questionnaires, and the things I naturally gravitate to were all part of this trip. The best way to describe it is MMT sent me someplace I didn’t even know I wanted to go! There was plenty to do, but I never felt rushed. Most memorable was the 18-mile bike tour to Sconset, sailing on the Endeavor, and my last night dining on the beach, wrapped in a blanket, watching the sun set and the stars come out.

What are your top tips for other potential mystery travelers?Stay flexible and be open to anything. Even if the destination is not what you expected or to your liking, it’s still a new experience and not to be wasted or taken lightly. And do not, under any circumstance, open the envelope until you get to the airport. While I feel certain I will do a MMT again, that first-time experience of “opening the envelope” cannot likely be duplicated…sort of like a first kiss.

Adventurous? Seen it all? Hate to plan? Want a Cinderella experience? Imagine, showing up at the airport and waking up in Morocco, or maybe Montana.

Impossible? Not a bit. Enter Denise Chaykun, president, and Stephanie Whitesel, executive director, of Magical Mystery Tours based in Washington, D.C. Travelers decide on a budget; how long they want to be away; fill out a detailed questionnaire about what they love, hate, don’t want, must have; and arrive at the airport with a secret-assignment package bound for who knows where. In advance, travelers are told what to pack and how they’ll get there. But if they can avoid peeking, the destination remains a surprise. Senior Secret Agent stuff.

Senior secret agent?? We’ll take it!

We really had fun doing this interview with Northern Virginia Magazine. We think that seniors (as well as most travelers!) have specific travel preferences and expectations, and shouldn’t hesitate to let their travel planners know about those desires. We’re more than happy to work with people who might have limitations in their diets, concerns about walking long distances, or other needs that can really make or break a trip.

If you’ve ever wondered what mystery travel is like and whether it’s for you, check out our new blog series, Mystery Traveler Q&A, in which we chat with some of our travelers about their experiences.

Ariana and Brett on their mystery long weekend in Montreal.

In late May 2014, Ariana and Brett headed to the Knoxville airport, ready for their long weekend mystery getaway. Upon opening their mystery packet, they discovered they were on their way to Montreal, Canada!

MMT: Why did you decide to take a mystery trip?A&B: We decided to take this trip because we loved the idea of being surprised at the airport with the destination! It seemed like such a fun and unique experience that we would remember for a long time. We only had a few days free to travel and so this seemed like a great time to try a mystery vacation and see if we liked it.

Did you have any guesses about your destination?Given the fact that we only had a few days, we assumed the destination would be in the U.S. or Canada. We were thinking either Colorado or Canada, but we tried not to guess so we could be totally surprised.

What did you like about doing a mystery trip?I loved the freedom to happily anticipate the upcoming vacation with no expectations and no neurotic searching of TripAdvisor, trying to plan out every minute of the trip. Often when we take a trip, I am exhausted by the time we actually leave because I’ve been trying to meticulously plan everything. It was great not knowing what to expect. We packed the day before based on the weather outlook and packing list provided and that was it! The only thing we could do was sit back and look forward to being surprised!

What did you do on your trip?We enjoyed walking all over Montreal, eating at some fantastic restaurants, shopping, getting lost, visiting several museums, going for a day hike, and seeing the newest Cirque du Soleil show. We were able to pack a lot into a short trip, but we had no set expectations, so we were able to just go with the flow and be spontaneous.

What are your other vacations like?We have traveled all over the U.S. and to various Caribbean islands, Mexico, etc. All trips have been planned ahead of time, sometimes at all-inclusive resorts. Sometimes we take last-minute trips to various U.S. cities for a long weekend. We enjoy sightseeing, hiking/outdoor activities, restaurants, museums, and golf and spa vacations.

What would you say to other travelers who are considering mystery travel?DO IT! It was such a fun experience, and MMT did an excellent job planning everything for us. I liked that we picked a short trip to start with, just to see if this was for us. Now I feel confident that we would love to do a longer mystery trip somewhere more exotic. Also, I would advise potential travelers to not try to guess the destination—you’ll ruin the surprise!

Such a fun list, and I’d say that Magical Mystery Tours is solidly in the middle of their “uniqueness” spectrum. Certainly crazier than a staycation or checking out your hometown, but a less crazy (and more affordable!) than space travel!

Thanks to Diane of Wife with Baggage for doing an interview with Magical Mystery Tours!

Here’s a little piece of the interview, but check out the whole post for more about our successes, nightmares, and some more travel tips!

Toot your own horn. What are you the most proud of when it comes to MMT’s successes?

“Knowing that we’ve helped people take vacations that otherwise never would have happened is such a great feeling. We love planning trips for everyone, though having a customer tell us that they just have no idea where to start and to trust us with a 25th anniversary trip or a trip to celebrate retirement or other huge life event is really special. We love getting to play a part in people’s big events!

I’m also really proud of our team of travel planners. Collectively, we’ve covered an awful lot of ground in our own travels and are really committed to finding whatever it is that’s the right destination for each traveler we work with. It would be much easier if we were just planning a bunch of trips to Vegas or Paris or Disneyworld, but we look at each traveler with a set of fresh eyes and really try to use our background to figure out what they’d love—and often that’s a destination that they may not have on their radars or might not have ever even heard of before!”

We have so much going on here at Magical Mystery Tours! Aiming to have many more posts coming soon, but here’s some of our big news:

We expanded (both geographically and in size)! We’re thrilled to have hired another travel consultant, Katie Truesdell (check out her bio on our about page). On top of that, Alicia just moved to London! We can’t wait to hear about even more European adventures she’ll surely be having. With Katie in Chicago and Alicia in London, this means that Magical Mystery Tours is now in Washington DC, Boston, Chicago, and London!

Stephanie’s still in Boston, but has a second little girl, Nalani, who was born in February.

Denise just got back from flying around the world. She stopped in Tokyo, Seoul, Thailand, and Frankfurt and will be posting the trip soon.

We’re also particularly excited about mystery trips that recently went out to Belize, Lisbon, Sedona, Dubai, the Dominican Republic, and a few other places. Of course, we’re also excited about mystery trips leaving soon, but that’s about all we can say about that!

Surprises, when done well, can be thrilling, even when it comes to something as personal and complex as travel. And . . . the building anticipation of mystery travel oftentimes gives adults the feeling of being kids on Christmas Eve. Not to mention, it nixes the stress of actually planning a vacation.

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